As a Sienese Senator, Pietro Marchese del Monte Santa Maria and Catherine formed their relationship early. Catherine wrote him four letters and it is clear that they had a sincere friendship. Catherine asked Pietro to help “the monastery of Santa Marta, whose members are perfect servants of God. The other concerns Monna Tomma,” she continues that, “I ask you lovingly to settle this as soon as you can, since they do not have much time.”1Catherine felt comfortable enough with their connection to ask for his help when needed. Also, Pietro was connected to Neri de Pagliaresi, remembered as Catheirne’s most devoted follower, and Niccolò Toldo, who was beheaded and then Catherine wrote her most well known letter detailing the execution. It is clear that Catherine saw Pietro as a man who had value to her work as a living saint, and saw it as her job to guide him on the proper path.